HCID 86690107, compound → HCID 86690108, compound

HRID 520399Notes

Reaction equation

HRID 520399 reaction equation
C([O:8][CH:9]1[CH2:14][O:13][CH:12]([C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][CH:9]1[CH2:14][O:13][CH:12]([C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 86690107HCID 86690107, compound

Product 1

HCID 86690108HCID 86690108, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-(benzyloxy)tetrahydro-2H-pyran-2-yl acetate (281 mg, 1.123 mmol) and ((1-methoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (783 mg, 4.49 mmol) in DCM (5 mL) at −78° C. was added BF3.OEt2 (0.228 mL, 1.796 mmol). The reaction mixture was gradually allowed to warm to rt and stirred at rt for 18 h. The reaction mixture was quenched with sat. NaHCO3 (5 mL) and diluted with DCM (20 mL). The organic layer was separated, washed with water, brine, dried (MgSO4) and concentrated. The crude product was purified by silica gel FCC (10-20% EtOAc in hexanes) to afford methyl 2-(5-(benzyloxy)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate as a colorless oil (253 mg). To a solution of methyl 2-(5-(benzyloxy)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate (250 mg) in MeOH (20 mL) was added 10% Pd—C (59.7 mg) and the reaction mixture was hydrogenated at 40 psi overnight. The suspension was filtered and the filtrate was evaporated to dryness to afford methyl 2-(5-hydroxytetrahydro-2H-pyran-2-yl)-2-methylpropanoate as a clear oil (188 mg).

Workup

  1. customwas hydrogenated at 40 psi overnight
  2. filtrationThe suspension was filtered
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9ec3ea0bbc8b4b60a19379151425baad
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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